Top 15 HUGE NHL Deals That Almost Happened

The history of the NHL is full of what ifs. Every fan asks themselves a question that begins with 'what if', in regards to the NHL. Whether it was what if Bobby Orr's knees didn't fail him, what if Wayne Gretzky was never traded, what if Brett Hull's Cup winning goal had been ruled illegal or what if the NHL had never expanded. Everyone loves asking these questions.

Another favorite topic of NHL fans is trades. Fans love to speculate about possible trades and they love digging up rumors from the past. For example, rumors have amounted in the past that Steve Yzerman was almost traded for Alexei Yashin or that Pavel Datsyuk was once sent to New Jersey for Scott Gomez.

What we'll be looking at today though, will feature deals, or transactions that almost went through. We're not necessarily talking about trades, although some rumored blockbusters were left in here. This one will be dealing with near-signings and non-hockey deals that almost shook the NHL. There'll also be plenty of offer sheets discussed, as many star players once signed with other teams as RFAs only for their previous teams to match it.

Here are 15 huge NHL deals that almost happened.

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15 David Backes To Vancouver

Aaron Doster-USA TODAY Sports

David Backes grew as the leader of the St. Louis Blues over the course of the last seven years, but there was once a time when the Blues almost lost their future leader to another team. Back in the summer of 2008, Backes was coming off his first full NHL season, having reached career highs of 31 points, with 13 goals and 18 assists. Unfortunately the Blues were a struggling franchise at the time and Backes signed an offer sheet as an RFA with the emerging Vancouver Canucks.

The Canucks signed Backes to an offer sheet of three years, worth $7.5 million. Being that the Canucks reached the Stanley Cup Final just a few seasons later, you'd have to think Backes could have helped that 2011 team that got pushed around by the Bruins. Unfortunately for Vancouver, the Blues knew what they had in Backes and quickly matched the offer.

14 Milan Lucic To The Montreal Canadiens

Jayne Kamin-Oncea-USA TODAY Sports

There was a time when Milan Lucic was just about the most hated player in the hockey Mecca of Montreal. Due to his years of service for the archival Boston Bruins, which included threatening several Habs players in a handshake line, following the 2014 Habs/Bruins playoff series, Montreal fans despised him.

This past summer though, Lucic and the Habs were very close to reaching an agreement. Lucic being a UFA, was actually offered more money from Montreal than the $42 million he took to sign in Edmonton.

“I had spoken to Montreal quite a bit actually, and that was one of the places – once the trade was made for Shea Weber – getting a chance to play with some B.C. boys with him, Carey Price and Brendan Gallagher that’s some good western boys, that’s something that really sparked my interest after that trade (Subban for Weber) happened,” Lucic told TSN.

13 Curtis Joseph To The New York Islanders

Toronto Star/Steve Russell

Back in 1998 Curtis Joseph was a pending UFA and the Edmonton Oilers were in financial peril as a franchise. Les Alexander had stepped in as a potential owner for the team, intending to move them to Houston. Cal Nichols and the Edmonton Investors Group had to worry about coming up with money to save the Oilers and knowing Cujo was going to command a lot on the open market, they seeked a trade partner.

Mike Milbury was running the show in Long Island and the Islanders were still searching for a long-term solution in goal. It's unknown what exactly was offered for Cujo, but a report from the New York Daily News had Rich Pilon and Tommy Salo going to Edmoton. Ultimately the trade never went through and Cujo signed in Toronto that offseason.

12 Artemi Panarin To Montreal

Aaron Doster-USA TODAY Sports

Artemi Panarin tore up the league last year playing alongside Patrick Kane, as the former KHL star came into the NHL and dominated, taking home the Calder Trophy. Panarin took less money from Chicago to sign with them, wanting to play for a Stanley Cup contender. The Montreal Canadiens had initially made overtures towards Panarin and it seemed like he was set to visit Montreal, which likely would have ended in a signing.

If Panarin had lost KHL conf final, would've visited Montreal. SKA erased 0-3 deficit, no visit, signed with Chicago https://t.co/ac9PYHqDcv

— Аrpon Basu (@ArponBasu) April 13, 2016

With Panarin's team down 3-0 in the KHL playoffs, the Habs heavily pursued him, making them the frontrunners to sign Panarin. However, Panarin's team would go on a run all the way to the KHL championship, which delayed the visit. By that point, more teams were after him and he ultimately chose Chicago.

11 Leafs And Oilers Swap Cities

via thestar.com

We're not just talking hockey deals anymore. We're talking about a huge business transaction that was discussed between the owners of the Toronto Maple Leafs and Edmonton Oilers. Harold Ballard and Peter Pocklington actually discussed their franchises swapping cities.

Pocklington explained in his book I'd Trade Him Again"  that Ballard was having financial problems in Toronto and made a proposal in 1980 for the Leafs and Oilers to swap cities, with Ballard gaining an additional $50 million.

Pocklington was very intrigued by the offer, as he had a young star in Wayne Gretzky on his hands and a dynasty in the making. Showcasing his team in Toronto would have been far more beneficial for him financially. Unfortunately for Pocklington, Ballard backed out at the last moment.

10 Sergei Fedorov To The 'Canes

via nhl.com

Sergei Fedorov was one of the elite players of the 90s and he quickly set many Red Wings franchise records. By the end of the 90s though, the relationship between Fedorov and Detroit management was on the rocks. Coming off a Stanley Cup championship in 1997, Fedorov held out for a new contract well into the 1997-98 season. Fedorov eventually signed an offer sheet with the Carolina Hurricanes worth up to $38 million. The Red Wings matched the offer.

The controversy of this deal came with a $12 million bonus payable if Fedorov's team reached the 1998 conference finals - at the time, the Wings were well on their way to competing for the Cup, while the 'Canes were at the bottom of the league. Obviously that posed a disadvantage for Detroit.

Nevertheless, the Wings paid the price and went on to repeat as Cup champions that year.

9 Thomas Vanek Signs With Edmonton

via zimbio.com

Remember when all teams were lining up to try to sign Thomas Vanek? Coming off the best season of his career in 2006-07, scoring 43 goals and 41 assists, Vanek was an RFA. The Oilers, looking to rebound after a disappointing season, signed Vanek to an offer sheet of $50 million over seven years.

After having already lost Daniel Briere and Chris Drury to free agency, there was no way the Sabres were going to let their young star Vanek walk as well. They matched the offer and Sabres GM Darcy Regier bashed Oilers GM Kevin Lowe, calling the move underhanded. Knowing how bad the Oilers have been for the last decade, it's very likely Vanek's career would have gone down the drain had he played in Edmonton.

8 Keith Tkachuk A Blackhawk

via espn.com

Keith Tkachuk was one of the bright spots on a Winnipeg Jets team that was struggling in the mid 90s and were on their way out of town. Prior to their final season in Winnipeg, the Jets' young star Tkachuk was an RFA, meaning he could sign with a team, with the Jets getting the right to match the offer.

Tkachuk got a front-loaded offer from Chicago and signed a five-year offer sheet with the Blackhawks, worth $17 million, with $6 million coming in his first year. With the franchise in such financial peril and an impending relocation to Phoenix, it wasn't expected that the Jets would match the offer. They did so just six hours later and Tkachuk remained in Winnipeg that season, moving along with the team to Phoenix the following year.

Seeing Tkachuk play with Jeremy Roenick in Chicago rather than Phoenix would have been very interesting.

7 Pat LaFontaine To Detroit

via espn.com

Pat Lafontaine was an exciting young prospect that grew up in the Red Wings' backyard. Going into the 1983 draft, the Wings fully intended to draft the hometown kid and give their long suffering fans something to cheer about. The Wings had the fourth overall pick, giving themselves a good chance to land him.

Unfortunately, a set of circumstances caused Lafontaine to be drafted just one pick before Detroit. Jimmy Devellano was in his first season as Wings' GM, but his old team, the New York Islanders, despite being defending champs, held the third overall pick. They had previously acquired the pick from the defunct Colorado Rockies. The Islanders stuck one to Devellano by taking Laftontaine. Luckily, the Wings had a great Plan B and drafted Steve Yzerman.

6 Harold Ballard Sells Frank Mahovlich

via alchetron.com

Harold Ballard had an extremely checkered history as Maple Leafs owner. He made many unpopular moves as Leafs owner but one of them was almost selling young superstar Frank Mahovlich. Coming off a Stanley Cup win in 1962, Ballard had a deal in place to sell Mahovlich to the Chicago Blackhawks.

On October 5, 1962, Hawks owner James Norris agreed to write a check to Ballard worth $1 million, higher than any price that had been paid for one athlete. It should be noted this offer was made after a night of heavy drinking.

Unfortunately, the deal fell through after Norris's brother Bruce, owner of the Red Wings, did all he could to kill the deal. Bruce Norris called Conn Smythe, the Leafs GM and let him know what was going on. Smythe didn't agree with Ballard trying to move Mahovlich and the deal was dead. Why didn't Bruce Norris want the Hawks getting Mahovlich? Well, he wasn't crazy about having to face a Blackhawks team comprised of Bobby Hull and Frank Mahovlich.

5 Shea Weber To Philadelphia

Aaron Doster-USA TODAY Sports

Shea Weber's current contract wasn't handed out to him by the Nashville Predators, but rather the Philadelphia Flyers. Had Weber been an RFA in any other offseason, it's very possible the 14-year, $110 million offer sheet he signed with Philly wouldn't have been matched.

In 2012 though, the Predators had their two best defencemen, Weber and Ryan Suter, hit free agency. The Predators lost Ryan Suter to free agency on July 1st, unable to match the 13-year, $98 million offer Minnesota gave him. Sensing that the Preds wouldn't pay a hefty price to keep Weber, the Flyers gave him that ridiculous offer.

The Predators had a week to match it and after five days, they elected to keep Weber, even if the price was high for a team running on an internal budget. Had Suter never left, it's quite possible the Preds would have been unable to pay Weber.

4 Teemu Selanne A Flame?

via manitobahockeynews.com

When Teemu Selanne first decided to play in North America for the 1992-93 season, he was an RFA, as he had not yet signed a contract with the Jets. The Jets' organizational philosophy at the time was to let their European draft picks develop in their native countries.

With Selanne as an RFA, the Calgary Flames decided to take a shot at the young Finn and signed him to an offer sheet worth $2.7 million, over double what the Jets had offered him. As we know, the Jets experienced a lot of financial troubles throughout their existence, which made them think twice about matching the offer. Ultimately, the Jets indeed matched the offer and Selanne went on to have a rookie season for the ages, scoring 76 goals.

3 Young Eric Lindros To The Rangers

via nbcphiladelphia.com

While Eric Lindros signed as a free agent with the New York Rangers later in his career, he could have been a Ranger all along had an arbitrator back in 1992 ruled differently. The Quebec Nordiques selected Lindros first overall back in 1991, but Lindros had no intention of playing in Quebec. The Nordiques had two deals in place for Lindros, one from New York and one from Philly.

The Rangers offered John Vanbiesbrouck, Tony Amonte, Alexei Kovalev, Doug Weight, three first round picks and $12 million.

An arbitrator, Larry Bertuzzi was to settle who would land Lindros. He chose the deal the Flyers offered the Nordiques, which included Peter Forsberg, Steve Duchesne, Ron Hextall, Kerry Huffman and Mike Ricci, a 1st round pick and $15 million. Bertuzzi would then rule that Chris Simon and a 1994 first rounder had to be included.

Just imagine if the Rangers got themselves a one-two punch of Messier and Lindros in the early 90s.

2 Mark Messier For Brett Hull

via nytimes.com / deadspin.com

Speaking of Messier, he was almost a part of a deal that would have seen two NHL icons being swapped. In the 1994 offseason, following the Rangers' Stanley Cup win, head coach Mike Keenan bolted for St. Louis. Following Keenan's departure, the Rangers and Blues were reportedly considering a mega-trade involving their captains.

Messier at the time was in a contract dispute with the Rangers, and was prepared to hold out. Brett Hull wasn't crazy about the idea of playing for a hard-nosed coach like Keenan. Glen Sather denied any reports of the discussed package. Eventually trade talks died down due to the lockout of 1994. The lockout gave the Rangers more time to sign Messier, which they did. The trade was dead because of it, but could it have happened?

Keenan and Messier reuniting would have made sense. It also would have been cool to see the free-spirited Hull in New York.

As we later found out, Hull was right for not wanting to play for Keenan and the Keenan/Messier duo did in fact reunite, but in Vancouver several years later.

1 Wayne Gretzky Signing With The Canucks

AP Photo/Ron Frehm

Following a disappointing tenure in St. Louis, the Great One was an unrestricted free agent in the 1996 offseason. Pat Quinn, the Canucks head coach at the time was in charge of negotiations and made a significant push for Gretzky.

“The Canucks had (Gretzky) signed at night verbally, and he (told Quinn), ‘Look. I’ll sign the papers formally in the morning,’ said Sportsnet’s Elliotte Friedman.

How did talks die down? A nosy owner. Orca Bay CEO Stan McCammon got on the phone with Quinn that same night and said he wanted the deal done that night. While Quinn tried to reason with the CEO that he had Gretzky's word, McCammon insisted: "No, no, no. We're doing this tonight. I want it formalized. No questions."

When Quinn called Gretzky back saying he wanted the deal done immediately, Gretzky felt uncomfortable with the situation and the deal blew up. As we know he ended up signing with the New York Rangers, where he'd end his career.

“It was a difficult summer. At one point I thought I was going to be a Vancouver Canuck and it fell through the wayside,” Gretzky said. “Everything happens for a reason, and I ended up signing with the New York Rangers… and truly enjoyed it.”

Oh, Canucks...

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